Process of preparing salts of the chloroethane sulphonic acid



Patented Nov. 22, 1932 o i d mam PRGCESS-OF PREPARING s; x or orrrionojsrnenn err Prronre Aer No Drawing Applieationfiz 1, 1939, Serial No. {178,545, and Germany Septemberfi, 1929.

The fpresent invention relates to a pr ooess 250' parts of crysteliized sodium sulfiteere of 'prepering jsalts of the chloroethene snl h parts of Water endlOO'pz rts phonic acid. v l I 1 y e nlcoholin a reflux nppsretus, the rev Weu have found thetjethyl'ene dichloride sel of which being made of copper, canbeca'used to react with solutions 'otsalte l ethylene chloride hasdisappearedi oi the sulfurous acid in such manner. that 1 ol and water ore then distilled and nizi-inly only one atom of chlorine isex' einnining seltis extracted With alcohol. changed 23nd salts of tneohloroethene "s lslim ie extract there is obtained a salt phonic" acid are produced. This 1" lli; .ng in laminae having a mother-ofquiteisurprising becaus esis known, each of i r; the contentof chlorine of the halogen e inn 7 be carried out With or Without the enth two Sins of ehlerine of r chloride is just as labile and exoheng, thefotheriwhich fact my beseen for in stance, fro the reactionwith :ill elie s or ciontlyo n aversi e115 8.5 percent; about oer centot' the salt consists of sodium 7 siilfonz te. This product is suffire for'inost reactions; by a repeated potassium cyanide.' V I r v v H lization from dilute alcoholit can" Contrary thereto it ispossible to obtain eesilyh'e freed from the admixed ethandi? ell defined salts of the "chloroethene 'sulsiil onate ainountingrto about 10 20: percent. phonic e'cid from ethylenedichloride and e 158 g. ofpotassiuinsulfite and 120 g.

re orystai.

- rnetalsalt or" thesulfurous acid bv causine' otf ethylenedich oride are heated to boilin i. v v r 7. V. v v 3 w suspended later-meme together at 'e teinou hly stirring, together with 1 200 cc. of perature' wh eh advantageouslydoes DQiJ'GX: Water and 400cc. of methanol to Which some ce ed 90,C.""A1nong' tlie substences- 'which zed copper lies been added. The re the two coiniionents in edissolved or finely for '3 hours in 1 reflux apparatus While thor may be used'es solvents, dilute aloe-bellies otion liqnid' is distilled until ethylenedii i c ride and Inethan no'long er pass over '5 id final yevaporated to dryness. 250' of dry substance containing lOper cent of lsiuin chloroethnne sulionart'e are ob- Q This crude product already be or many re otions; By exti action with el there is obtained therefrom the pure sium echloroetha'ne sulfonete crystalliz- "colorlesslsminee. 16 i ofni flesiuinsulfite and 1205;; pljcg fion of a raised pressure, ylene bOlld fO 20 llOlll The metal salts of the ohloroethene sulin the reflux apparatustogether With 2 liters phonic acid thus obtained bodies who; 0" Waterend ()"c-e. or": m thanol. The un crystallize Well and are Valuable intermediate ng p g y" 903111339 g fi S111? been foundto be appropriate. ln'ord r to acoelerate the rezilctionQthe reaction in conduotedin the presence of e-ni metal compound capable eeeele Xchenge, such as copper; copper chloride'or berium chloride. It isndvsntegeous to use an excess of ethylene dichloride in order to avoid as farssipossib the formation of ethane disulfonhtesi he reaction products for introducinginto conigminds for ilto i isenmfetoe'by filtering by suction and. a

instance, into dyestuffs containing hydroxy then-nets then treated esdescribed in EX- groups or amino groups the residue of the nlple The crude nt anet obtained 'oonethane sulphonic acid, the ethyl sulfo group ma nesium- Chloloethene Sulfonete for conferring on the compound a good solu niey likewise be obtained in" a pure bility. The free chloroethene sulohonie aoie Stet-e of extraction of the product With alco or the chloride thereoi may he obtnined from 1101. I I e Y the salts accordlng to known general methods. 4;) inenner analogous to that de- The followlng examples serve to illustrate scribed n. the or see examples 195 9'. 0i?

i the invention, but they are not intended to crysts llze'e zinc white and 120 of ethylene limit it thereto, the parts being by Weight: dichloride 7 re boiled ror 20 hours together (1.) 100 parts of ethylene dlchloridennd WrthlSOOCc. of Water and lOO cc. ofinethanol to which some copper sulfate has been added. The unchanged zinc sulfite is then separated by filtering by suction. Methanol and the excess of ethylene dichloride are distilled and the whole is evaporated to dryness. The crude product obtained contains 85 per cent of Zinc chloroethane sulfonate which may be purified as usual.

We claim: I

1. The process which comprises causing a solution of ethylene dichloride to react, while refluxing the vapors evaporated from the reaction mixture, with a solution of a sulfurous acid salt of a metal selected from the group consisting of Na, K, Ca, Mg, at a temperature below 90 C., wherein ethylene dichloride is used in excess, and then separating the chloroethane sulfonate produced.

. 2. The process which comprises causing an aqueous alcoholic solution of ethylene dichloride to react, while refluxing the vapors evaporated from the reaction mixture, with an aqueous alcoholic solution of a sulfurous acid salt of a metal selected from the group consisting of Na, K, Ca, Mg, at a temperature below 90 C. wherein ethylene dichloride is used in excess, and then separating the chloroethane sulfonate produced.

. 3. The process which comprises causing an aqueous alcoholic solution of ethylene dichloride to react, while refluxing the vapors evaporated from the reaction mixture, with an aqueous alcoholic solution of a sulfurous acid salt of a metal selected from the group consisting of Na, K, Ca, Mg, at a temperature below90 C. in the presence of a metal catalyst accelerating the halogen exchange and selected from the group consisting of copper, copper chloride andbarium chloride wherein ethylene dichloride is used in excess, and then separating the chloroethane sulfonate produced.

4:. The process which comprises causing an aqueous alcoholic solution of ethylene dichloride to react, while refluxing the vapors evaporated from the reaction mixture, with an aqueous alcoholic solution of sodium sulfite at a temperature below 90 C. in the presonce of a metal catalyst accelerating the halogen exchange and, selected from the group consisting of copper, copper chloride and barium chloride, wherein ethylene dichloride is used in excess, and then separating the chloroethane sulfonate produced.

5. The process which comprises causing an aqueous alcoholic solution of ethylene dichloride to react, while refluxing the vapors evaporated from the reaction mixture, with an aqueous alcoholic solution of sodium sulfite at a temperature below 90 C. in the presence of copper metal, wherein ethylene dichloride is used in excess, and then separating the chloroethane sulfonate produced.

6. The process which comprises causing a suspension of finely divided ethylene dichloride to react, while refluxing the vapors evaporated from the reaction mixture, with a suspension of a finely divided sulfurous acid salt of a metal selected from the group consisting of Na, K, Ca, Mg, at a temperature below 90 0., wherein ethylene dichloride is used in excess, and then separating the chloroethane sulfonate produced.

7 The process which comprises causing an aqueous alcoholic suspension of finely divided ethylene dichloride to react, while refluxing the vapors evaporated from the reaction mixture, with an aqueous alcoholic suspension of a finely divided sulfurous acid salt of a metal selected from the group consisting of Na, K, Ca, Mg, at a temperature below 90 C. wherein ethylene dichloride is used in excess, and then separating the chloroethane sulfonate produced.

8. The process which comprises causing an aqueous alcoholic suspension of a finely divided ethylene dichloride to react, while-refluxing the vapors evaporated from the reaction mixture, with an aqueous alcoholic suspension of a finely divided sulfurous acid salt of a metal selected from the group consisting of Na, K, Ca, Mg, at a temperature below 90 C. in the presence of a metal catalyst accelerating the halogen exchange and selected from the group consisting of copper, copper chloride and barium chloride wherein ethylene dichlorideis used in excess, and then separating the chloroethane sulfonateproduced.

9. The process which comprises causing an aqueous alcoholic suspension of finely divided ethylene fluxing the vapors evaporated from the reaction mixture, with an aqueous alcoholic suspension of sodium sulfite at a temperature below 90 C. in the presence of copper metal, wherein ethylene dichloride is used in excess, and then separating the chloroethane sulfonate produced. V

In testimony whereof, we aifix our signatures.

': OTTO ERNST.- OTTO NICODEMUS.

dichloride to react, while res 

